


a length of rope

by LoveIsNotAVictoryMarch



Category: Supernatural
Genre: Alternate Universe, Alternate Universe - Human, Alternate Universe - Pirate, Historical Inaccuracy, M/M, Officer Castiel, Period Typical Attitudes, Pirate Dean, vaguely inspired by black sails
Language: English
Status: In-Progress
Published: 2018-01-28
Updated: 2018-03-17
Packaged: 2019-03-10 14:01:07
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 4,638
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13503035
Author URL: https://archiveofourown.org/users/LoveIsNotAVictoryMarch/pseuds/LoveIsNotAVictoryMarch
Summary: Castiel Milton comes to the Caribbean to hunt monsters in human disguise, pirates that defy the laws of the British Empire. He’s a man who needs rules to keep his life in balance, a man who cherishes order and despises anything that disturbs it. Enter Dean Winchester, a pirate captain who will eventually turn Castiel's life upside down.





	1. prologue

**Author's Note:**

> So here it is, my new WIP. As always, I have a rough outline and will try to update once a week if life allows it. I chose the explicit rating because I know me, but it's possible I'll change it back to M as the story progresses. The story is inspired by Black Sails but you don't have know it to follow the plot. There might be quite a few geographical and historical inaccuracies in this - sorry for that. I've planned for around 10 to 12 chapters, but it might get longer than that. If you hop on the train, let me know what you think, will ya?

The first thing they see isn’t the bright linen of sails nor the dark spot of a ship’s hull. It’s the smoke that billows up from the horizon, a white patch in the clear blue sky. Cas squints against the sunlight and tries to make out the source of the white cloud, when the man high above him in the crow’s nest shouts: “Pirates!”

That first shout travels over the ship, is repeated in ten, twelve voices until the captain emerges from his cabin, closes his red coat, brushes a few crumbs from his lapels and orders, “Set a course.”

Cas heart flips in his chest. He’s been to war, has been decorated even for his bravery and prowess in the fight, but this… He’s never seen a pirate, only heard the tales his older brother told and the ones the magazines back in England published; tales of gruesome murderers, thieves without a conscience, sodomites without faith or honor. 

Their vessel picks up speed. It’s a frigate of the Royal British Navy, 50 guns and 150 men on board, all of them experienced pirate hunters. After Cas landed in Boston, the vessel took him on to deliver him to his brother Michael, governor of Charleston. The sails above him bellow as they catch the wind, men run around him shouting orders, and Cas stands in the middle of the turmoil and feels his stomach drop with every mile they come closer to the pirates. 

He’s just a passenger on this ship, forced to stand by and watch, as his uniform lies neatly pressed in his crate down in his cabin. Cas swallows against the tight collar of his shirt and reaches up to scratch under it. He should be happy that he can forego a wig while travelling, but the civilian clothes are just as stifling. He can do nothing but stand still and let the officers around him steer their course. His right hand twitches at his side where his saber uses to sit. He curls his fingers until his nails bite into his palm and tries to calm his breathing.

Now he can see the two ships lying close to each other. The smoke is gone and opens the view to a large and a smaller ship. 

“They caught a merchant ship,” the captain says next to him. Cas didn’t hear him approach. “Thank god we took this route. If we’re quick, we’ll get those bastards and send them back to the hell they crawled out of.” The captain’s mouth is a thin line full of righteous hatred. Cas nods. 

“Have they seen us yet?”

“Let’s hope they’re too busy ransacking the hold of the merchant to look up and watch the horizon.” The captain takes out his glass and brings it to his right eye. “No such luck, I’m afraid.” He closes the looking glass and turns to his crew. “Faster! They’re getting away!” 

The last two sails fall toward the deck and snap like bullets in the wind. It might give them half a knot more, but Cas doubts they will catch up with the smaller ship if the pirates get a head-start. He can see the deck of the pirate vessel bustling with activity now. By now large knives will cut loose the ropes that tie the ships together. Men climb up the rigging like ants to ready the topsails. 

“Ready the guns!”, the captain shouts next to him, and Cas can feel the rumble underneath his feet as the men open the ports and roll back the cannons. The sails of the pirate ship open and catch the wind. At first the movement is nearly imperceptible, but then the ship lurches, turns into the wind and picks up speed fast. 

A yell knives through the air. “Fire!” 

The front cannons blast their deadly cargo in the direction of the pirate vessel. Three shots only meet the waves, a fourth rips away large chunks of the brig’s stern in a cloud of splinters. Cas sees a figure standing on deck in the middle of the carnage, unmoving. Broad shouldered, clad in black, like a figment of a dream, quiet between the debris and the smoke. Above him, the black flag flutters in the breeze. 

Cas narrows his eyes to make out more details, because this is the first pirate he sees in person and Cas wants to commit the image to memory. The figure is too far away to see his face. Cas’ fancy fills in the blanks from all the pictures he’s seen of the monsters that haunt the seas between the Americas and Jamaica. In his mind, the pirate captain comes to life, with a scarred face and a nasty snarl curling his lips, demonic green eyes filled with hatred and bloodlust. Cas swears to himself that he will bring this one to justice. 

The distance between the ships grows rapidly. The pirates are already out of range. As Cas predicted, their captain decides against pursuing the brig. The Navy vessel slows down to stop next to the merchant ship, an old galleon with serious damage all over its side. Cas can sees small fires on at least three points of the deck when they get close, which are furiously fought by several men, but the flames already lick up the main mast and will soon reach the first sail. The ship is lost. The captain comes to the same conclusion. 

“Don’t get us too close. Set out boats to take the crew on board,” he barks, and in a flurry of motion the vessel is stirred to a safe position and men lower the long boats into the water. An hour later the merchant crew is assembled on the deck of the Navy vessel and watches their ship go up in flames. 

“Set sail. Bring us to Charleston.” The shout travels over the ship like an echo,  _ setsail _ ,  _ setsail _ , until the crew is up in the rigs again and the ship turns into the wind to leave the site. Cas goes over to the captain of the merchant ship, a burly old man with grey hair and a big belly. There are grease stains on his worn coat, and his lapels are dark with grime. He brings the stench of burning wood with him. They shake hands and Cas notices that the captain’s still tremble slightly. 

“We’re lucky you came by,” he tells Cas. “They were just done hauling the cargo unto their ship and might have killed us all after that. Or we’d gone up in flames with our ship.” 

Cas nods. “Who was it? Did you recognize the crew?”

“Oh, I didn’t have to. Captain Winchester introduced himself when he took over the ship. We surrendered after the first shots had left severe damage. He sauntered on board, congratulated me for my wise decision, and told his men to spare my crew.” 

Cas arcs an eyebrow at that, and the captain shoots him a bitter smile. “But you know, that means nothing. The moods of pirates shift like the sea, and they are devious to the bone. Many a crew has been told they would be spared and then killed in cold blood. Dead men tell no tales, that’s their motto. Never make the mistake to trust this scum.”

Cas hangs on the man’s lips, a strange mix of horror and excitement swirling through him. This is what he came here for. To hunt pirates and bring them to justice. To restore peace and safety in the area under the rule of the British Empire. And he already knows where he’ll start. The silhouette of a broad-shouldered man rises up from his memory.

He’ll start with Captain Winchester. 


	2. family dinner

**Notes for the Chapter:**

> So, new chapter. Warning for Michael being a period-typical bigoted asshole in this and some violent images, though nothing too graphic. Let me know what you think?

 

 

Charleston is bustling with life and commerce. It’s not a proper town by English standards, not more than a cluster of wooden houses and dirt streets, but Cas can see the signs of civilization everywhere. In a few decades it will be a flourishing city. He walks through the busy streets from the harbor to the market square. In the middle of the open space sits a wooden dais, and on it a structure not unlike a gallows with a metal cage attached. It’s the most prominent point of town, surrounded by crows that pick away at the remains of a pirate. 

Cas slows his pace to look at the nearly unrecognizable figure. He must have hung in the sun for a few weeks already. His clothes are in tatters, white bones peek out from under the cloth, and his skull is almost plucked clean. The metal of the cage squeaks with every soft breeze that comes up from the ocean. Cas knows why this is necessary – people have to see the consequences of piracy after all – but the image makes him shiver. It’s one thing to hang a man for his crimes or sentence him to hard labor, it’s another thing to make him a spectacle like this. 

Despite the warmth of the day, there’s still a cold spot between his shoulder blades when he arrives at his brother’s house north of the market square. It’s the first brick building he’s seen, with wide glass windows and three polished steps leading up to the front door. Cas ascents the stairs and knocks on the door. A servant opens after the fourth knock. 

“Can I help you, sir?”

“Yes, my name is Castiel Milton. I’m here to see my brother, the governor.”

He’s lead to a sunny parlor with a view over the generously planned gardens out back. Flowers he’s never seen before are in full bloom, and their scent wafts over through the open windows. There’s a stunning beauty to this place, amidst all the violence and the bloodshed. Cas thinks back to the man hanging outside in the square, a stark contrast to the quiet peace of the scene in front of him. Cas walks over to admire the vista for a few minutes before he hears a door opening behind him. 

“Castiel. We expected you at least one day earlier.”

Cas turns to greet his brother. They shake hands, short and firm, and he finds no trace of warmth in the features of his older brother. He’s never seen Michael anything other than this: controlled, stern, calculating. 

“Michael, it’s good to see you. We had to make a detour as we happened to interrupt a pirate ambush on a merchant ship.”

Michael’s brows draw together, but he doesn’t seem the least bit curious about the story. All he says is “Those damn bastards”, before he reaches for a bell on the table and rings it. 

Only moments later two slave girls enter with silver plates heaped with steaming food. “Since you came in late, we’ll have dinner now. You can change into fresh clothes later.” 

Cas would have loved to wash himself and change his clothes after weeks at sea, but he knows better than to contradict his brother. With a court nod he sits down at the table. Michael tells him his wife and daughter are gone to visit some relatives while the slaves fill their plates and pour the glasses. Cas thanks them under his breath. He’ll have to get used to this. 

At home, they always had servants, so he’s used to people waiting on him, but this is different. His brother owns these people, and Cas is not sure he will ever be able to just accept that. He knows better than to mention it, though. He had this conversation with Michael before who had told him in no uncertain terms that this was a necessity and the conquering of the New World came at a price. That, in the end, their servants at home only had an imagined freedom because they, too, had little to no chance to not work for the Lords. Cas found both of these arguments lacking. But he was new here, didn’t have the experience his brother had, and in these matters, opposing him was out of the question. 

He concentrates on the food, which is easy since it’s delicious. Spicy herbs, vegetables and soft meat make up the dish, and after eating only stew on board for weeks, the fresh meal is highly appreciated. He swallows a low moan when he takes the first bite of a tasty slice of bread. His stomach already aches from the amount of food and he forces himself to chew slowly and savor each bite. 

“One could think you almost starved to death, little brother. Did the Navy not take good care of you?”

Cas swallows carefully. “Yes, they did, but you know how fresh food is a rarity on every ship.” Cas lifts his head to smile and show his appreciation for the invitation, but Michael doesn’t look at him as he shoves his plate away. 

“I would pay good money for a good English stew. I’ve had enough of all these foreign fruit for a while.” His mouth is drawn into a thin line of distaste. It angers Cas that his brother is able to sit amidst such luxury and still find fault in it somehow. He takes another bite in silence. 

“You’ll tire of this so-called New World soon enough, little brother. Scratch the surface and it’s nothing but grime and filth out here.” Michael leans back and staples his fingers over his softening belly. “So tell me, what are your plans?”

“I’ve been offered a position with the governor in Port Royal,” Cas says and braces for his brother’s answer. It comes immediately. 

“As what? A simple soldier? I could have gotten you a post in one of the Companies, or you could work with me here as my right hand.” Michael looks offended by the mere thought, but Cas is determined. 

“I want to learn about this place and work my way up like every other man. And I won’t be one of his soldiers, I’m taking the position of Governor Romans’ late Lieutenant.” He tries to keep the ice out of his voice, and pushes the rising anger down. Fighting with his brother won’t change their stances on the matter - he knows that from experience. Michael knows, too. After a moment of drawn-out silence, Michael sighs. 

“You and your childish notion of honor. I suppose I won’t change your mind. Father will be most disappointed.” He wipes his greasy fingers on a pressed linen napkin and claps his hands for the servants to clean the table. Cas swiftly picks up on last bite of the delicious vegetable before his plate is taken away. A girl not older than fifteen enters and sets a crystal bottle filled with an amber liquid on the table, along with two heavy glasses. Michael pours them both a generous drink, and Cas takes the offered glass gratefully. The sting of alcohol tickles his nose, but he travelled with Navy soldiers for a few weeks, so he’s used by now to the strong liquor. 

“To the Milton family,” Michael says, and lifts his glass. 

“To the family,” Cas answers, clinks his glass to his brothers and takes a long drink. The rum burns in his throat and settles hot in his stomach. All of a sudden, the strain of the last weeks catch up with him and his limbs grow heavy with fatigue. The prospect of a proper bed instead of a cot on a Navy vessel makes him yearn to retire and sleep for a few days. 

He finishes his drink and starts to rise. “Thank you for your hospitality, Michael. If you don’t mind, I’ll go to my room now.”

Michael nods benevolently. “I’ve had the guest room on the first floor made ready for you. Should I send you a girl upstairs?”

Cas’ brain is dizzy with the alcohol and his tiredness, so he needs a moment to get the meaning of Michaels’ words. “A girl?” he asks, dumbfounded. 

“Yes, Castiel. There’s upsides to the life here.” With a s sweeping gesture he points at the maids in the corner of the room. Cas looks over at them and takes in their stoic expressions. The youngest, the one who brought the rum earlier, can’t quite hide the fear in her eyes. Yet, Castiel thinks with horror. His stomach lurches when he fully comprehends what his brother is offering and he leans heavy on the table to gather his bearings. 

“No,” he chokes out. The thought to spend a night under his brother’s roof has suddenly lost its appeal and he can’t wait to leave this place behind. He’s disgusted with the mere idea of treating human beings this way, and for all the differences Michael and he had over the years, this makes him regret every time he gave in and put their brotherly bond first. “No, Michael, I don’t want you to force any of your slaves into my bed,” he grates out, his whole body shivering with rage. 

“Oh, again with your silly idealism,” Michael chuckles. “Or maybe the offerings just don’t cater to your tastes, hm?” 

Cas contemplates punching the mean grin right off his brother’s face. His hands curl into fists and it takes all his strength to straighten and turn, to leave the room without another word. 

He’s bone-tired when he sinks into bed after undressing and cleaning up, but sleep evades him. He tosses and turns on the too-soft mattress, going over the conversation with Michael again and again and with it all the implications his brother left unsaid. When dawn breaks and casts the sky in red, orange and purple, he rises, packs his few belongings and slips out of the house. There’s a merchant vessel leaving for Port Royal in the morning and Cas intents to be on board. 

 

 


	3. the governor

 

 

Sir Richard Roman took his post as governor of Port Royal 15 years ago. He made it the most successful venture in the New World, and his name became interchangeable with cunning opportunism in London. His methods, on the other hand, were only discussed in whispers. Cas never gave much weight to rumors. As a military man, he knows victory always comes at a price, and he is determined to make up his own mind about his new boss. 

Port Royal is stifling hot when he arrives. The air is heavy with humidity and a thousand unfamiliar scents. The island is all bright colors, overwhelming his senses from all sides. His shirt sticks to his back immediately and he curses his heavy coat while he finds his way through the narrow streets. People make room when they see him coming, but they don’t cast down their eyes, follow his every step with barely disguised mistrust and hatred. 

The governor resides a ways out of town in his mansion. From there he leads his men, most of whom are stationed at the fort that looms over the sprawling labyrinth of Port Royal. Cas leaves the bustling town centre and finds a stable to rent a horse. The owner of the stable looks him up and down, bushy grey eyebrows drawn together in a calculating grimace, and Cas lets himself be weighed and judged for a minute, before he grows impatient.

“Sir, I am in a bit of a hurry. Do you have a horse to lend? It’s only for the afternoon.”

“You’re new,” the man grumbles, still not moving, still analysing Cas’ appearance. It’s not a question, but Cas answers right away. Manners are hard to leave behind. 

“Yes, I am. I need to visit the governor. Would you be so kind to get me a horse ready?” While his words are perfectly friendly, his tone might not be. He’s tired and the drying sweat starts to itch on his temples and his throat, and he doesn’t have the time for this. 

“Hmmmpff,” says the stable master, but he turns and points to one of the boxes on the right. Behind the waist-high wooden door, Cas can see a light-brown mare with kind eyes. He goes over and pets the soft nose while he listens to the rustling behind him. The stable-master readies as saddle and the stirrings. 

“How did you know?” Cas asks. “That I’m new.”

The old man passes him and opens the door. Cas waits while he works with stiff but experienced hands, watches as the horse calms down with every small pat on his flanks. Cas wonders if the stable master forgot his question. When the saddle is fastened and Cas grabs the reins to mount the horse, the man finally answers. 

“There’s still kindness in your eyes.” He tips his non-existent hat and claps the mare on her backside. Cas tightens his grip and concentrates on steering the horse out of the stable, too flummoxed to answer. 

Cas didn’t know how much he missed riding until he feels the strong muscles of the horse working under him and the wind on his face as he gallops down the road and puts mile after mile between him and the town of Port Royal. Left and right he’s greeted by the artificial landscape that comes only with hard labor in these parts of the world. A week, a month without weeding the fields will bring back the jungle. 

The sun burns on his neck and here, where nobody sees him, he opens the top button of his coat to allow the fresh air in. For a moment, he wishes he could just ride on, never stop, until he finds a patch of land no soul ever set foot on, a place somewhere deep in the woods where he can live on his own and forget all about the so-called civilized world. 

He shakes his head as if he could clear the thought from his mind that way. The memory of the burning merchant ship is still fresh, and he holds onto it. He has a mission here. From the green surrounding him rises a white formation in the distance that grows into the outline of a huge house, a mansion really, set on a small hill, overlooking the fields with the lazy arrogance of the British aristocracy. 

Slaves work in the gardens and raise their face to get a look at him while Cas passes, but nobody greets him. He slows his mare to a trot and rides up to the house to unmount and tie the reins to one of the posts next to the steps. The sun still burns on his back, but it can’t stop the nervous shiver that crawls over his skin when he takes in the sheer mass of the house and its cold atmosphere. Maybe he’s lived on ships for too long, encased by wood, in close quarters with too many men, that he can’t appreciate this kind of open living spaces anymore. 

The massive door is opened by a maid after his third knock. Cas feels the grime on his sweat-slick skin and rubs over his forehead in a nervous gesture. Certain that this will makes things worse he lowers his hand to his side and nods politely at the maid. He is led to a large room at the end of a wide hall. Every detail of the house is oozing splendor. Gold framed-art clusters the wall, pieces that speak more of money than of taste, and Cas works to keep from frowning. There’s appreciation of the art and there’s telling others that they’re far below your station. This is the latter and Cas does not approve. A governor does well to make his position clear, but he doesn’t have to flaunt this kind of luxury in the faces of those he governs. The man he’s about to meet will not share the sentiment, Cas is sure of that, so he presses his lips together in a thin line and keeps his eyes to the ground. 

Every prejudice he might have had from the gossip in London and the first impression of his home is validated during the twenty minutes he spends in Richard Romans study. When he is dismissed Cas mounts his horse with instructions to take his post at the fort near town and assume the tasks of the first lieutenant. Keep order in town and the soldiers in line. 

He navigates his horse down the pathway that leads to the road with a gentle nudge of his knees. Back under the relentless sun he’s sweating again. With a grunt he fastens the reins on his saddle and slips out of his coat, bundles it up and bends down to stuff if into his saddle bag. The light breeze is cool on his soaked skin and makes him sigh with relief. He tugs his shirt out of his trousers and lets it billow around him.

When he looks up again, a figure in horseback approaches from the west, galloping over the soft hills. Cas turns his mare to the road but watches the rider curiously. His control over the massive black stallion is impressive, his posture straight and speaking of practice and a fundamental understanding of horses. The rider slows down when he reaches the pathway and gets close enough for Cas to recognize him. The welcomed coolness of his skin turns into ice. 

This is the second time they see each other. The closer distance shows Cas mossy green eyes, a cloud of freckles on finely sculpted cheeks and full lips currently stretched into a grin. The man doesn’t seem to know who he is, but Cas is sure he’s facing the infamous Dean Winchester, would know those broad shoulders everywhere since that day on the ship. 

Cas’ face must barely conceal his disgust, but Winchester’s smile doesn’t falter. He tips a finger to his non-existent hat and turns into the pathway to the governor’s house.  _ Evil disguises itself with the most beautiful faces _ , his aunt had told him when he was a boy. Even now, even knowing what he knows about this man, he can’t keep his eyes away, still stares when that pirate captain reaches the door and vanishes in the house with long, confident strides. 

“What about the pirates?” Cas had dared to ask when the governor had fallen quiet after rattling down Cas’ new duties. Roman had looked up with a calculating expression. 

“What about them?”

“What steps should I take to bring them to justice?” Cas had faced him calmly, shoulders squared. This was what he came here for. 

“Let that be my concern, Lieutenant Milton.” Roman had stared at him, and when Cas didn’t answer, he had looked down at the papers in his desk, the dismissal clear. 

_ Let that be my concern _ . It seems that his superior wasn’t all that concerned about the pirates at all, when he met with one in open daylight, invited him to his house even. Cas hands curl into fists until the leather of his reins cut deep into his palms. Anger rolls in his gut like a stone, makes him nauseous. He is standing at a moral crossroads, mere hours after his arrival. When he reaches the town he can’t remember a single thing about the ride. The old man in the stable takes one look at him, grunts, and keeps his mouth shut. Cas’ sour mood must be written clearly on his face. 

The rest of the evening goes by in a flash. He greets his new subordinates, inspects his office and his quarters at the fort and falls into a restless sleep as soon as his head hits the pillow. 

Cas is up with the sun the next morning, full of energy and filled with the liberating lightness of a decision made. 

“Bradbury,” he orders one of his young sergeants, “bring in Captain Dean Winchester. I want to have a word with him.”

 

 

**Author's Note:**

> I'm [procasdeanating](WWW.procasdeanating.tumblr.com) on tumblr. Come say hi!


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